Cellulosic composition of matter containing ethyl cyclopentanone carboxylate



Patented Oct. 4, 1932 UNITED "stares PATENT OFFICE THOMAS P. MURRAY, JR., Annc RrL J. s'rAUp, or RoenEs'rER', New YORK, AssIeNoRs 'ro EASTMAN KODAK COMPANY, or ROCHESTER, NEW YORK, A CORPORATION on NEW YORK CELLUIiOSIG COMPOSITION OF MATTER CONTAINING ETI-IYL 'CYCLOPENTLANONE' I i CARBOX'YLATE No Drawing. 7

This invention relates to compositions of matter in which cellulose derivatives, such as cellulose acetate, cellulose nitrate, or cellulose ether, are comblned or mixed with '1 other substances, such asa compatible plasticizer, and a common solvent for both, with or without other useful'addition agents, so

that the resulting product will have prop-' manufacture of wrapping sheets, photo grapic film, artificial silk, varnishes'or lacquers',and the like.

-One object of this invention is to produce a composition of matter which may be made.

into permanently transparent, strong and flexible sheets or films of desired thinness which are substantially waterproof, are unaffected by ordinary photographic fluids and possessthe desired properties of a support for sensitive photographic coatings. An-

other object of our invention is to produce a composition which is capable of easy and convenient manipulation in the plastic and analogous arts, such as in the manufacture of sheets, films, artificialsilkfilaments, varnishes, lacquers and the like, andto produce a composition which will'not injure, or be injured by, the substances orsurfaces with whichit is associated during manufacture. Other objects will become apparent to those skilled in the art to which this invention pertains;

While cellulose acetates, nitrates and ethers have been known for decades it has also been known that to utilize them in the various plastic arts it is necessary to mix therewith such plasticizing or conditioning agents as camphor, castor oil, triphenyl phosphate, monochlornaphthalene or' the like. Certain of these and other addition agents are also added for the purpose of reducing the infiammability of the product.

-Plastic inducing'agents, such as the higher alcohols and their esters, are sometimes also added. Similarly, addition compounds of various kinds have been employed to increase flexibility, transparency, toughness and other properties which will enhance the Application filed September 12,1930. Serial No.481,584.

value of the resulting product. Addition products for the same or similar purposes are, also added to cellulose acetates, nitrates and ether's to prepare them for use in the other plastic arts, such as in the manufacture of lacquers, varnishes, artificial silk filaments, moulded compounds and the like. While the plasticizers ior otherv addition agents heretofore discovered have had their utility in theart, the increasing use of which cellulose derivatives have been put and the increasing number of desirable properties requiredof the :cellulose derivative for most purposes has made the discovery of new and economical plasticizers or other addition agents a matter of considerable importance to the art.

We have discoveredthat valuable properties may be induced inand/or contributed to, compositions containing cellulose derivatives, such as cellulose acetate, by adding thereto the plasticizing'compound ethyl cyclopentanone carboxylate together with a solvent, such as acetone, whichwill dissolve both the cellulose derivative .and plasticizer, This plasticizer has the structural formula Ila l1:

It is compatible with cellulose derivatives and particularly compatible withcellulose acetate in the percentages hereinafter given. It is not an expensive compound and not particularly difiicult to produce, or obtain upon the cpen market'; The particularly useful properties which it induces in or contributes to a cellulosiccomposition'containing it arehereinafter enumerated. 1 In order that those skilled in this art may better understand our inventionlwe :would state, by way of illustration, that for the manufacture of photographic film. or other sheets our new compositionof matter may be compoundedas follows 2100 parts" of acetone soluble cellulose acetatei. e. cellulose acetate containing from 38% to 42% acetylradical,. approximately, .is dissolved with stirring: at

atmospheric temperature in 300 to 500 parts, preferably 400 parts, by weight, of acetone. To this solution may be added from 10 to parts by weight, of ethyl. cyclopentanone carboxylate, it being foundpr'eferable to employ approximately 30 to 4.0 parts thereof, lVit-hin the limits stated, the amount of plasticizer may be decreased or increased, depending upon whether it is desired to decrease or increase, respectively the propertieswhich this plasticizer contributes tothe finished product. The amount of solvent employed may also be decreased or increased, depending upon whether-it is desired to have a more or less freely flowing composition, respectively, and in fact theethyl cyclopentanone carboxylate is itself a solvent for cellulose acetate, for instance, and will re duce or even eliminate, if desired, the amount of acetone or other common solvent normally employed. I

A composition of matter prepared as above described may be desposited upon any suitable film forming surfacexto form afilm or sheet, as is-well known to those skilled in the art. A film soproduced has permanently brilliant transparency and low inflammability, burning no more readily-than ordi nary newsprint. Such film is exceedingly tough and flexible, as shown by the fact that it will withstand many folds upon a modified Schopper fold-tester (commonly used for such purposes). withoutbreaking and that even after being subjected for a considerable number of days to air maintained at a tem-- perature of 65 C. theifilm. still maintains flexibility (in contrast to almost complete lack of flexibility where no plasticizer is used) demonstrating that the filmwill withstand ordinary usage satisfactorily for many years. Thelsum total of the above advantageous properties of aproduct produced from our new composition is considerably in excess of that of products produced with 5 what have previously been regarded as the better plasticizers.

Other similar solvents (instead of acetone) which are compatible with the cellulose acetate and our new plasticizer may also occur to those skilled in this art. Inlike'inanner: this plasticizer may be compounded with other single organic esters of cellulose, such as cellulose Ipropionate, butyrate and the like, or with mixed organic and/or inorganic esters, such ascellulose aceto-stearate, acetomalate, or cellulose intro-acetate, or with thecellulose ethers,a suitable solvent which will dissolve both the cellulosic derivative and the;

plasticizer beingemployed.

Inasmuch as our above described composi tion of matter is quite useful in the production of films and sheets it will be apparent that our new plasticizer may also be employed with advantage in the other branches of the plastic art. For instance, 'our above described composition of matter may be em" ployed in the manufacture of artificial silk by the dry spinning method. With the proper coagulating bath it may also be employed for wetspinning. It may be desired to employ a composition of different viscosity or evaporation characteristics but this is a mere matter of changing the solvent proportion or adding evaporation retardents or other high or intermediate boiling constituents, as has been Well known in the art for more than a decade' Our novel plasticizer'may also be employed with advantage in connection with a number of the :known lacquer and varnish formulae with which it may be found to be compatible. In-such cases the plasticizer is usually first put-into solution with the cellulose derivative solution and if non-solvents are added for the purpose of cheapening the composition they are added only to such an extent as will not precipitate the derivativefrom solution. Also the plasticizer is'usually employed in larger amounts, such as from 50 to 60 parts, in compounding lacquers.

Other uses Within the scope of our'invention will also sug'gestthernselves to those skilled in the art and are to be included within the scope of the claims appended hereto.

What we claim as our invention, and desire.

to be secured by Latters Patent of the United States, is: 1

1. A composition-of matter comprising a cellulose derivative and ethyl cyclopentanone carboxylate. r r

2. A composition of matter'comprising cellulos'e acetate and ethyl cyclopentanone carboxylate.

3. A composition of matter comprising 

